The Dip - Should you fold or double down


New things start fun, but once the new wears off they are hard because of the Dip. The Dip is the long slog between starting and mastery. Unlike Dips, cul-de-sacs are places you can put in a lot of energy and nothing will come of it. You need to quit cul-de-sacs and lean into dips. Much of our failure comes from being distracted by tasks we don’t have the guts to quit. Winners quit all the time. They quit the right stuff, so their energy can be saved to cross the Dip.

Get The Dip to learn if you should be doubling down, or looking around.

Be great

Being well rounded is bad

  • Average is invisible is replaceable
  • Better to be bi-modal, double down on things your great at, skip things you’re bad it.
  • If you’re going to be the expert, double down on the things that matter there.
  • If you hit all the check boxes, you’ll probably lose to someone that’s worse at the check boxes, but nail the thing that matters.

Be the best in the world

  • Best is way more valuable then second best, see Zipff’s law.
  • Best in world is subjective - best in eyes of beholder. They define the what best means, and what world means.
  • World is bigger in that distribution is free.
  • World is smaller in that niches can find perfect matches.

Good quitting

Quitting is really important.

  • Finite energy, infinite outlets: Impact = energy/things => Too many things, no impact.
  • Better only do things where you can have impact - this means you won’t be doing something else, that will hurt - live with it.

You need to quit cul-de-sacs and dips that you can’t cross

A special cul-de-sac: Needing to influence a single person/organization for success.

If you need to influence your boss/organization to be successful and you haven’t after several tries, there’s a decent chance you’re in a cul-de-sac. If this person/organization has built a perception of you and your work, even as you and your work changes for the better, this person/organizations perception will not. It’s much easier to influence the market where each new person is a fresh start where your previous errors can be forgotten. As a simple analogy, what’s more likely to succeed marrying the first girl you get a crush on, or getting married to any woman that you meet?

Quitting Before You Start

Deciding in Advance When to Quit

If you’re not going to get to #1, you might as well quit now.

Quitting a Tactic vs. Quitting a Strategy

That Noise Inside Your Head Quitting as an Intelligent Strategy Quitting Is Not the Same as Failing Coping Is a Lousy Alternative to Quitting “Never Quit” Pride Is the Enemy of the Smart Quitter Harvard Medical School Is Not a Reason to Stick (Ignore Sunk Costs!)

Soft Tires Pick Your Dip You’re Astonishing The Best in the World? It’s Almost Impossible to Over invest in Becoming the Market Leader. Share the Dip

Bad quitting

Can I make it through the dip?

Serial Quitting

Reactive Quitting

Kinds of Dips

These Dips are in the places where you’ll want to give up. If you see these Dips coming, you’re more likely to make a choice. You can choose (in advance) to do whatever you need to do in order to get through the Dip, knowing it’s going to be difficult; or you can give up before you get there. Quitting in the Dip, though, isn’t worth the journey.


The combination of bureaucracy and busywork you must deal with in order to get certified in scuba diving. The difference between the easy “beginner” technique and the more useful “expert” approach in skiing or fashion design. The long stretch between beginner’s luck and real accomplishment. The Set of artificial screens set up to keep people like you out.


A career gets started as soon as you leave school. But the Dip often hits when it’s time to go learn something new, to reinvent or rebuild your skills. A doctor who sacrifices a year of her life for a specialty reaps the rewards for decades afterward.


When it’s all about you, it’s easier. Giving up control and leaning into the organization gives you leverage. Most people can’t do this; they can’t give up control or the spotlight. They get stuck in that Dip.


There are people and organizations that can help you later but only if you invest the time and effort to work with them now, even though now is not necessarily the easy time for you to do it. That kid who started in the mail room—who was always eager to do an errand for you or stay late to help out—she’s now the CEO. The relationships she built when it was difficult to do so paid off later. Those shortsighted people who are always eager for a favor or a break never manage to get through the relationship Dip, because they didn’t invest in relationships back when it was difficult (but not urgent).


You got this far operating under one set of assumptions. Abandoning those assumptions and embracing a new, bigger set may be exactly what you need to do to get to the next level. The heroes who have reinvented institutions and industries (everyone from Martin Luther King, Jr., to Richard Branson, from Zelma Watson George to Jacqueline Novogratz) all did it in exactly the same way—by working through a conceptual Dip all the way to the other side.


Most ideas get their start when one person—you—starts selling it. Selling the idea to stores or to businesses or to consumers or even to voters. But the Dip hits when you need to upgrade to a professional sales force and scale it up. In almost every field, the competitor that’s first with a big, aggressive sales force has a huge advantage.

Taking a loan

Bootstrappers learn the hard way that at some point they can’t pay for it all themselves, especially out of current income. It takes a risk to rent a bigger space or invest in new techniques. Successful entrepreneurs understand the difference between investing to get through the Dip (a smart move) or investing in something that’s actually a risky crap shoot.


Some retailers (local strip malls, the Web) make it easy for your product to get distribution, while others (Target) require an investment from your organization that may just pay off. Getting your product into Wal-Mart is far more likely to lead to huge sales than is putting it on the Web. Why? Scarcity. Everyone is on the Web, but getting into Wal-Mart is hard.


It’s easy and fun to start building something in your garage. It’s difficult and expensive to buy an injection mold, design an integrated circuit, or ramp up for large-scale production.

I don’t know where I stand

Is this a Dip, a Cliff, or a Cul-de-Sac?

Who do I need to influence?

If it's a single person/organization, you'll probably fail. If it's a market, keep trying.

Is my persistence going to pay off in the long run?

What chance does this project have to be the best in the world?

When should I quit?

I need to decide now, not when I’m in the middle of it, and not when part of me is begging to quit.

I think I’m in a DIP

Should I really be calling on IBM? Should I really be trying to get on Oprah?

Does it make sense to submit a resume to every single ad on Craigslist, just to see what happens?

Can we make the world smaller?

I think I’m in a Cul-de-Sac

Need to quit if you’re branded by your co-workers/bosses.

How can I change it into a Dip?

Am I engaged with just one person (or organization)?

Do my actions in this situation spill over into the entire marketplace?

If I quit, will it increase my ability to get through the Dip on something more important?

Is there something dramatic I can do instead of quitting that will change the game?

I want to quit

Am I panicking?

If you’re panicking, not the time quit. The time to quit is at the point you decided it was time to quit.

How do you know it’s time to quit? Because you pre-planned the quitting criteria. Go read that part again.

Who am I trying to influence?

If it’s a single person/organization, you’ll probably fail. If it’s a market, keep trying.

What sort of measurable progress am I making?

Again, set the criteria go from there.

I feel too comfortable

Are you avoiding the remarkable as a way of quitting without quitting?

If you like your job, is it time to quit?

Is doing nothing better than planning on quitting and then doing something great?

Are you scared?

Are you settling